US11505566B2ActiveUtilityA1

Organic metal compound and organic light-emitting device

53
Assignee: IND TECH RES INSTPriority: Jul 23, 2018Filed: Jun 24, 2019Granted: Nov 22, 2022
Est. expiryJul 23, 2038(~12 yrs left)· nominal 20-yr term from priority
C09K 2211/185C07F 15/0033C09K 11/06H01L 51/0085H10K 2101/10H10K 85/342H10K 50/11
53
PatentIndex Score
0
Cited by
34
References
8
Claims

Abstract

Organic metal compounds and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II):In particular, one of the following two conditions (1) and (2) is met:(1) R1 is deuterium or C1-6 deuterated alkyl group, when R3 and R4 are independently hydrogen, halogen, C1-6 alkyl group, C1-6 fluoroalkyl or C3-12 heteroaryl group; and(2) R1 is hydrogen, deuterium, C1-6 alkyl group, C1-6 deuterated alkyl group, C3-12 heteroaryl group, or C6-12 aryl group, when at least one of R3 and R4 is C6-12 aryl group or C6-12 fluoroaryl group.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. An organic metal compound, which has a chemical structure of Formula (II): 
       
         
           
           
               
               
           
         
       
       wherein X is O or S; R 1  is hydrogen or deuterium; R 2 , R 4  and R 5  are hydrogen; R 3  is phenyl group; R 9 , R 10 , R 11  and R 12  are independently hydrogen, halogen, deuterium, C 1-6  alkyl group, C 1-6  deuterated alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11  and R 12  are optionally combined with the carbon atoms which R 9 , R 10 , R 11  and R 12  are attached to, to form an aryl group or a cycloalkyl group, wherein R 13 , R 14 , R 15  and R 16  are independently hydrogen, halogen, C 1-6  alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15  and R 16  are optionally combined with the carbon atoms which R 13 , R 14 , R 15  and R 16  are attached to, to form an aryl group or a cycloalkyl group. 
     
     
       2. The organic metal compound as claimed in  claim 1 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
       
       wherein R 1  is hydrogen or deuterium; R 2 , R 4  and R 5  are hydrogen; R 3  is phenyl group; R 9 , R 10 , R 11  and R 12  are independently hydrogen, halogen, deuterium, C 1-6  alkyl group, C 1-6  deuterated alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11  and R 12  are optionally combined with the carbon atoms which R 9 , R 10 , R 11  and R 12  are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16  are independently hydrogen, halogen, C 1-6  alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16  are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16  are attached to, to form an aryl group or a cycloalkyl group. 
     
     
       3. The organic metal compound as claimed in  claim 2 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
       
       R 2 , R 4  and R 5  are hydrogen; R 3  is phenyl group; R 9 , R 10 , R 11  and R 12  are independently hydrogen, halogen, deuterium, C 1-6  alkyl group, C 1-6  deuterated alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11  and R 12  are optionally combined with the carbon atoms which R 9 , R 10 , R 11  and R 12  are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16  are independently hydrogen, halogen, C 1-6  alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16  are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16  are attached to, to form an aryl group or a cycloalkyl group. 
     
     
       4. The organic metal compound as claimed in  claim 2 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R 1  is hydrogen or deuterium; R 2 , R 4  and R 5  are hydrogen; and R 3  is phenyl group. 
     
     
       5. The organic metal compound as claimed in  claim 1 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
       
       wherein R 1  is hydrogen or deuterium; R 2 , R 4  and R 5  are hydrogen; R 3  is phenyl group; R 9 , R 10 , R 11  and R 12  are independently hydrogen, halogen, deuterium, C 1-6  alkyl group, C 1-6  deuterated alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11  and R 12  are optionally combined with the carbon atoms which R 9 , R 10 , R 11  and R 12  are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16  are independently hydrogen, halogen, C 1-6  alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16  are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16  are attached to, to form an aryl group or a cycloalkyl group. 
     
     
       6. The organic metal compound as claimed in  claim 5 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
       
       R 2 , R 4  and R 5  are hydrogen; R 3  is phenyl group; R 9 , R 10 , R 11  and R 12  are independently hydrogen, halogen, deuterium, C 1-6  alkyl group, C 1-6  deuterated alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11  and R 12  are optionally combined with the carbon atoms which R 9 , R 10 , R 11  and R 12  are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16  are independently hydrogen, halogen, C 1-6  alkyl group, C 1-6  fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16  are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16  are attached to, to form an aryl group or a cycloalkyl group. 
     
     
       7. The organic metal compound as claimed in  claim 1 , wherein the organic metal compound is 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R 1  is hydrogen or deuterium; R 2 , R 4  and R 5  are hydrogen; and R 3  is phenyl group. 
     
     
       8. An organic light-emitting device, comprising:
 a pair of electrodes; and 
 an organic light-emitting element disposed between the pair of electrodes, 
 wherein the organic light-emitting element comprises the organic metal compound as claimed in  claim 1 .

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